


Pain Lies On The Riverside

by DeanstielsDaughter



Category: Supernatural
Genre: Almost Drowning, Blackmail, Crobby - Freeform, Darkfic, Gen, Hurt/Comfort, M/M, Oneshot, Tricking Demon, Twisted Romance, lying
Language: English
Status: Completed
Published: 2015-08-31
Updated: 2015-08-31
Packaged: 2018-04-18 09:35:40
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,235
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4701086
Author URL: https://archiveofourown.org/users/DeanstielsDaughter/pseuds/DeanstielsDaughter
Summary: <blockquote class="userstuff">
              <p>"And just why did you cut him slack?" the crossroads demon asked Crowley. "It's simple really," Crowley said. "He's different." Bobby Singer, who was practically baptized in whiskey, knew better than to make a deal with any demon, much less a demon as powerful as Crowley.</p>
            </blockquote>





	Pain Lies On The Riverside

"So put your feet in the water, put your head in the water, c'mon put your soul in the water…join me for a swim tonight!" – Live (Pain Lies on the Riverside)  
-8-8-8-8-8-8-8-8-8-8-

Bobby Singer sighed and sat at his old wooden kitchen table with a look of disdain. Dean and Sam had just left and his house was once again filled with an overwhelming silence. Sure most times he preferred to be alone, but after having company on whatever terms he missed the sound of other voices besides his own after said company left.

Bobby poured himself another glass of Jack Daniels and gulped half of it down. The shadows coming from outside his windows were a bit more unnerving than ever before. He didn't know why, but he could only sense deep in his gut, something wasn't right somewhere. His neighbors would've dismissed that as nonsensical worrying. Most people looked at him and saw nothing more than an old drunken kook or a barely functioning alcoholic. He had so few living friends, but that didn't bother him so much. He preferred the company of his boys and his bottles and he truly didn't care what others thought of him.

Bobby stood from the table and was about to call it quits for the night when that unnerving feeling hit him again, straight deep in his bones. He heard a small crash somewhere in the woods and a manly cry following it. He grabbed his gun and cocked it, bolting from the house out the back door and into the woods.

He wasn't concerned with someone intruding on his land; he could easily take care of that with a single bullet. He was more worried about whether or not someone was hurt. Bobby hadn't taken this path into the woods in quite a long time, not since Sam and Dean were kids. He remembered taking them to the lake and setting up a tire swing for them and fishing for hours on end instructing them just how to reel in what they'd caught. Those were the good old days. Bobby felt the fallen red and gold leaves crunching underneath his boots and he readjusted his cap before spinning around once, his gun poised high and ready to fire.

He saw nothing.

He heard the moan of pain once again coming in the direction of the far side of the lake and Bobby took off. If the person was injured they'd need help right away and he couldn't just leave them there in pain. Bobby picked up the pace until he reached where the cries had come from and he about rolled his eyes, scratch that he did roll his eyes, when he saw who was lying there.

"Well if it isn't Bobby Singer," Crowley smirked, but winced when he moved, grabbing his blood covered side. "Look what the cat dragged in."

"I should be saying the same thing to you Crowley," Bobby glared. He was about ready to shoot the bastard on site, Crowley was vulnerable and hurt that would've made it easy. Something though, told Bobby not to. "What messed up your ass so badly?"

"Well I don't mean to intrude but I had to cut trough these woods to get to my next deal," Crowley laughed painfully. "Needless to say another one of my demons took care of it after some backwoods drunk assumed I was a bear or something and shot me."

"They weren't that far off." Bobby laughed.

"Making jokes at my expense love?" Crowley scoffed. "Why that's not nice at all."

"Who said I was a nice person," Bobby inquired and bent down to inspect the wound that had formed on Crowley's side. "You're hurt pretty bad."

"Thank you for those words of obvious wisdom Mr. Singer," Crowley sarcastically replied and more blood gushed out of his side. "Really I thought it was just a flesh wound."

"Look ya ungrateful ass you want my help or not?" Bobby was starting to get annoyed.

"Seeing as I have no other choice…" Crowley sighed.

Bobby helped the King of Hell to his feet and the pair shuffled back to Bobby's house through the dark woods. The feeling Bobby had received in his gut earlier never went away completely, but it had lessened a bit. His gun banged against his back as Crowley painfully limped along with the hunter down the backwoods trail and onto Bobby's property. Tears welling up in his eyes with every step he took. It was the closest to human Bobby had ever seen him be.

Bobby shut the door behind both of them and locked it, re-salting the windows and drawing another devil's trap on the door.

"I take offense to that you know." Crowley flatly stated and Bobby ignored him before he trudged to his bathroom to get the necessary supplies and then went back to the living room where Crowley was currently bleeding out on his couch.

"And I should care why?" Bobby replied and started cleaning the wound and stitching Crowley up. He poured some whiskey on the cut and Crowley cried out only once before Bobby started to run the needle through the wound to make stitches.

"That's why I always liked you Mr. Singer," Crowley smirked. "You've got a sense of humor, unlike those boys of yours, they've got sticks up their asses till Tuesday. Are they around?"

"No so it's your lucky night," Bobby said. "Because if they were here you'd have a barrel of salt filled gun up your ass."

"I'm quivering in my knickers." Crowley chuckled.

"Just shut up for a minute alright?" Bobby glared and continued fixing him up until the wound was sewed shut and disinfected and Bobby was wiping his bloody hands on a dirty dishrag. He could've smacked himself silly right then and there, helping a demon? Much less Crowley? That was basically suicide. When had he gone so soft?

"I suppose I do owe you one." Crowley said, his voice lowering a bit as if he couldn't believe the words he was saying. "You did just save my life."

"Don't mention it. In fact please don't mention it ever." Bobby grudgingly replied and drank some more whiskey; he knew he'd have to be drunk to have this conversation.

"Mr. Singer you underestimate me," Crowley sat up slowly, still clutching his side but he was careful not to break the stitches. "I'm not in this for anything; I simply wish to repay you for all you've done for me."

"What's the catch?" Bobby was certainly skeptical, this was Crowley after all. The one and only "stab in you in the back" asshole demon that could easily ruin a life in a moment.

"For anyone else, their life." Crowley stated. "For you? No catch. I happen to like you Mr. Singer."

"I can't tell if that's a good thing or a bad thing." Bobby rolled his eyes a bit and drank the rest of his glass.

"When enemies are many and allies are few you'll be glad you made this deal." Crowley replied. "It's just a simple proposition."

Bobby Singer, who was practically baptized in whiskey, knew better than to make a deal with any demon, much less a demon as powerful as Crowley. Something told him otherwise though, a part of him wanted to high tail it out of that room and run, but the other part, the stronger part, beckoned him to stay.

"Fine, speak your peace Crowley." Bobby replied, glaring at the King of Hell.

"I wish to issue a challenge to you Mr. Singer," Crowley explained. "You seal a deal with me, no strings attached, I'll send my hellhound after you in ten years. If you can kill and escape my hound I'll be your servant for as long as you require me and I shall do any bidding you wish."

"And why in the Sam Hell would you wanna do that?" Bobby asked skeptically.

"Because I like you," Crowley replied. "You've got guts and I admire that. So do we have a deal or don't we?"

Bobby thought about what Crowley was proposing for a moment. Sure, it'd be great to have the demon as his bitch, but as always Bobby knew there was a price. Crowley was right though, with the upcoming war and all that jazz allies would be hard to come by, so if he could just string Crowley along until all of that was over it'd be worth his while.

"Deal." Bobby finally replied, before sealing it with a regretful kiss.

-8-8-8-8-8-8-

Nine years later…

"You've gone soft Crowley." A crossroads demon spoke behind his King who was eagerly watching the show as the souls were thrown into Hell. Crowley never got tired of watching that. "Letting that Singer guy get off easy, his time is almost up you know that right?"

"I made a deal and I'm sticking with it." Crowley grumbled. "If he could kill off my Hell hound that I send to kill him then I'd be his servant for as long as he pleased. Demons can't back out of deals you know that."

"Why him?" the crossroads demon asked, he was honestly a bit confused on the whole ordeal.

"He's special." Crowley said breathlessly.

"You like him." The demon replied. "You know what happens when we make attachments in this life Crowley. They end up dead and in line."

"He's different this man won't give up the fight, for that I admire him." Crowley explained. "I just want him to know that even if I'm not on his side I still believe in him."

"If you believe in him that much," the demon laughed a horrible cackle in his home environment that would've been much quieter and tamer on earth. "Tell him to stop drinking; I can practically feel his liver deteriorating from down here!"

Crowley ignored the demons wheezy laughs and continued to stare at the hell fire. In one short year he'd have to send his hound after Bobby Singer. He hadn't lied when he'd said he admired the man, liked him even. He hated to do that. Deals couldn't be broken though and he knew that firsthand.

He just hoped that when Bobby finally had to stand in the line before him, he wasn't there to witness it.

-8-8-8-8-8-8-

One year later

Bobby Singer panted hard and gritted his teeth. He was covered in blood and dirt from wrestling the creature, but he had won. He was victorious against Crowley's hellhound and he couldn't have been more proud of himself. He set his gun down and looked at the pool of blood in front of him leaking from the invisible dog's body and smirked, kicking a bit of dirt at it.

"That the best you got old man?" Bobby scoffed and looked upwards before he heard a rustle of leaves behind him.

"Well played Singer," Crowley said. "Well played. You killed my mutt."

"That was the deal wasn't it?" Bobby replied. "And now you're my bitch. Must feel degrading."

"I'm actually not affected by this at all, it doesn't change things." Crowley stated.

"Still I got you by the manhood practically," Bobby smirked. "And you have to do everything I say."

"Careful now Bobby," Crowley smirked playfully. "Too much power can go to one's head. Anyway I suppose that was my bargain now wasn't it? So what is it you require of me?"

Bobby thought long and hard about that and finally replied.

"Make sure the angels don't win this one." Bobby narrowed his eyes. "Lucifer can't destroy the earth and he can't have Sam end of story."

"I'll do my best Mr. Singer." Crowley nodded and then disappeared without a trace leaving nothing but the whisper of the leaves behind him.

-8-8-8-8-8-8-

Many months later…

The war was over. Sam was freed, but at what price? Sure, he'd gotten his soul back from the pit but he'd never be the same, not with the memories from Hell always on the verge of spilling into his mind. Dean was distraught and Bobby just felt lost. There was nothing left for him anymore. He'd drunken every bottle of Jack Daniels, rum, and whiskey in his house and it still wasn't enough for him to be comfortably numb. This was the most vulnerable and depressed Bobby had been in a long time.

He was currently sharpening his knife and taking little sips from his glass. His eyes were a haze. He breathed shallowly and slowly. He felt older than ever before and every bit of him ached from various emotions. He sharpened the knife much too quickly and it sliced his palm and it was dripping blood.

"Balls!" he exclaimed and grabbed a clean towel to apply pressure with.

He turned his head to see a figure walking into the woods. The figure turned and smirked at Bobby, leaving him a bit baffled. It was Crowley. He'd almost forgotten the man existed after the war between Heaven's two biggest angels was over with. That bastard had lied to him! He'd promised he'd keep Sam from getting hurt and he'd lied!

Bobby growled as Crowley disappeared back into the woods towards the river and the lake behind Bobby's property. Bobby, though still bleeding but he ignored that, grabbed his shotgun and chased after the demon.

-8-8-8-8-8-

"You think Bobby's okay?" Sam asked Dean, the pair were driving towards his house after having completed a rather tedious case. "He was so upset and angry after all this, I wouldn't be surprised if he…"

"Sammy," Dean reassured his brother. "He would never do anything that drastic."

"Dean," Sam sighed. "He's old, he's seen a lot of messed up shit in his time, I honestly wouldn't put it past him."

"You're wrong Sammy," Dean flipped open his phone and started to dial Bobby's number. "He always answers and this time he will too."

Dean dialed the number, the phone rang.

Bobby didn't answer…

"I'm sure he's just…busy…" Dean was trying to convince himself otherwise.

"Dean…" Sam bit his lip.

Dean hit the gas so hard he was sure it broke at least five world records.

-8-8-8-8-8-

Bobby knew this was a bad idea. He knew nothing but pain would come if he went to the river. That's where Crowley was, but something beckoned his feet forward and he found himself there. It was quiet, a dark but warm night and the breeze blew softly. The leaves crunched and flew through the air with ease. The trees were casting ominous shadows and the moon shone so bright it could've been used as a second sun. There, Bobby waited.

"Decided to play hide and seek Mr. Singer?" Crowley finally appeared with a shit eating grin on his face. The moonlight cascaded over his features and Bobby felt vile even being in his presence.

"You!" Bobby growled. "You ungrateful, sorry, son of a bitch! You PROMISED me Sam wouldn't be harmed!"

"I promised you I'd try." Crowley glared. "I never promised you a rose garden Bobby dearest."

"You're still a liar…" Bobby sighed; he was so sick and tired of playing people's games.

"You seem spent Bobby," Crowley cocked his head and walked closer, circling the man. "Are you tired Bobby Singer, do you just wish for it all to be over?"

Bobby looked downward, a sullen look on his face. It was true, he'd been through more than enough shit to last a lifetime and sometimes he did just want it all to be behind him.

"I admit it yes Crowley," Bobby replied softly. "I do."

"I thought you'd never ask." Crowley whispered, hauntingly close to Bobby's ear making the hairs on his neck stand on end. Crowley walked away from him and to the river's edge, snapped his fingers once and a small portal begun to open up, the water's surface quivering and shaking. "Come swimming with me? I know you'll enjoy it."

Crowley's smirk was like Medusa. Tainted and evil, but impossible to look away from at the same time.

Bobby stepped forward. His feet went first, the water lapping at the soles of his boots. He went in a bit deeper after that, up to his knees. Crowley's smirk growing bigger and bigger every second.

"That's it Bobby," Crowley said, almost hypnotically. "Join me where you belong."

-8-8-8-8-8-

Dean and Sam pulled up and bolted out of the Impala guns poised and adrenaline pumping. They burst through the front door and took in the room around them. Dean stepped into the kitchen and looked down at the floor where the blood was pooled.

"Bobby…" he muttered. "Bobby you stupid bastard…"

His head shot up when he heard the banging of Bobby's back screen door against the door frame and a leap of hope settled in his chest. He motioned for Sam to follow him and the pair made their way to the woods where the followed the drops of blood and footprints towards the river.

-8-8-8-8-8-

"I've been waiting for this for awhile Bobby," Crowley said as Bobby became more and more submerged in the river water. "Soon you'll be with me forever in the pit where you belong, you'll finally be dead Bobby, and you've wanted that for awhile haven't you? You've picked up that gun so many times only to put it right back down because you weren't strong enough. I can help you Bobby, I can help you do what you've always wanted to do."

"Sounds nice Crowley," Bobby replied, getting close to the man himself. "That sounds really nice…"

"So do we have a deal?" Crowley asked, smirking. The portal's mouth ominously glowing behind him. It was a straight shot to the underworld.

"Sorry but," Bobby smirked. "I've got too much to live for!"

He pushed Crowley hard and he flew back into the portal which sucked him back into Hell with a blood curdling scream. Bobby shut his eyes as a flash of light blasted through the woods and the portal closed. He fell backwards at the riverside and breathed heavily.

"As for you," Bobby said to Crowley, wherever he'd been sent. "Consider you position as my bitch repealed!"

Bobby then stumbled to his feet and picked up his gun.

"Bobby!" Dean yelled through the trees as he and Sam ran to where the older hunter was standing, gun in hand. "Oh Bobby Jesus Bobby you gave me a damn heart attack!"

"What are you two idjits doing here?" Bobby asked. "Not that I'm ever not happy to see ya."

"You didn't pick up so we gunned it here," Sam explained. "We know you've been unhappy for awhile and then we saw the blood and we just…"

"We wrongly assumed that you'd…" Dean bit the inside of his lip.

"You two are damn fools do you know that?" Bobby chuckled. "I just pushed a damn demon back into Hell because he thought I wanted to kill myself and offered to help me. I led him on and now he's gone so ya'll two don't have to worry about me. As for the blood I just cut my hand ya idjits."

He showed them his palm and Dean smiled relieved.

"We're glad you're okay Bobby." Sam nodded. "And we're glad you didn't go with that demon. We kind of need you."

"Oh c'mon boys," Bobby smirked. "I'm not that stupid."

**Author's Note:**

> Reviews are appreciated!  
> Title inspired by the song Pain Lies On The Riverside by Live


End file.
